The iodine-catalyzed cascade reaction of -formylarylketones with indoles for the synthesis of indolylbenzo[]carbazoles is reported. The reaction is initiated in the presence of iodine by two successive nucleophilic additions of indoles with an aldehyde group of -formylarylketones, and the ketone does not undergo a nucleophilic addition and only involves in the Friedel-Crafts-type cyclization. A variety of substrates are tested, and the efficiency of this reaction is demonstrated with gram-scale reactions.
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http://dx.doi.org/10.1021/acs.joc.2c02868 | DOI Listing |
J Org Chem
March 2023
Department of Chemistry, National Taiwan Normal University, No. 88, Sec. 4, Ting-Zhou Road, Taipei 11677, Taiwan, Taiwan, R.O.C.
The iodine-catalyzed cascade reaction of -formylarylketones with indoles for the synthesis of indolylbenzo[]carbazoles is reported. The reaction is initiated in the presence of iodine by two successive nucleophilic additions of indoles with an aldehyde group of -formylarylketones, and the ketone does not undergo a nucleophilic addition and only involves in the Friedel-Crafts-type cyclization. A variety of substrates are tested, and the efficiency of this reaction is demonstrated with gram-scale reactions.
View Article and Find Full Text PDFChem Commun (Camb)
June 2020
Department of Chemistry, University of Delhi, Delhi 110007, India.
An efficient and BF·EtO-catalyzed chemoselective synthesis of diversified 1,3-diarylisobenzofuran in a high yield has been described. The reaction proceeds through sequential hydroarylation-cyclization between 2-formylarylketones and electron-rich arenes/heteroarenes. Advantageous features of the developed methodology include operational simplicity, a broad substrate scope, and applicability towards gram scale synthesis.
View Article and Find Full Text PDFOrg Lett
May 2012
Department of Chemistry, University of Cologne, Greinstr. 4, 50939 Köln, Germany.
The surprisingly facile conversion (isomerization) of 2-formyl-arylketones into 3-substituted phthalides, as observed for the marine natural product pestalone and its per-O-methylated derivative, was investigated using a series of simple 2-acylbenzaldehydes as substrates. The transformation generally proceeds smoothly in DMSO, either in a Cannizarro-Tishchenko-type reaction under nucleophile catalysis (NaCN) or under photochemical conditions (DMSO, 350 nm).
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